KR890700117A - Anti-ulcer agents and novel chalcone derivatives containing chalcone derivatives as active ingredients - Google Patents

Anti-ulcer agents and novel chalcone derivatives containing chalcone derivatives as active ingredients

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KR890700117A
KR890700117A KR1019880700971A KR880700971A KR890700117A KR 890700117 A KR890700117 A KR 890700117A KR 1019880700971 A KR1019880700971 A KR 1019880700971A KR 880700971 A KR880700971 A KR 880700971A KR 890700117 A KR890700117 A KR 890700117A
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Prior art keywords
propanone
carboxymethoxy
group
isopentylphenyl
methoxyphenyl
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KR1019880700971A
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Korean (ko)
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고마자와 유끼오
다께다 시게후미
호사까 구니오
와따나베 도시히꼬
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쓰무라 아끼라
쓰무라 준펜도 인코포레이티드
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Priority claimed from JP29495286A external-priority patent/JPS63150241A/en
Priority claimed from JP19819787A external-priority patent/JPS6442422A/en
Application filed by 쓰무라 아끼라, 쓰무라 준펜도 인코포레이티드 filed Critical 쓰무라 아끼라
Publication of KR890700117A publication Critical patent/KR890700117A/en

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    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음No content

Description

유효성분으로서 칼콘 유도체를 함유하는 항 궤양제 및 신규의 칼콘 유도체Anti-ulcer agents and novel chalcone derivatives containing chalcone derivatives as active ingredients

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (6)

유효성분으로서 다음의 일반식(Ⅰ)의 화합물을 함유하는 항궤양제Anti-ulcer agent containing a compound of the following general formula (I) as an active ingredient 상기 일반식중, X 및 Y는 각각 수소원자를 나타내거나 함께 단일결합을 형성하고, R'1은 히드록실기, 아세톡시기, 카르복시메톡시기 또는 메톡시카르보닐메톡시기를 나타내고, R'2는 수소원자, 이소프레닐기, 이소펜틸기 또는 프로필기를 나타내며, R'3은 히드록실기 또는 메톡시기를 나타내고, R'4는 수소원자, 히드록실기 또는 메톡시기를 나타내고, R'5는 수소원자, 히드록실기, 메톡시기 또는 이소펜틸기를 R'6은 히드록실기, 메톡시기 또는 카르복시메톡시기를 나타내며, R'7은 수소원자 또는 메톡시기를 나타낸다.In the general formula, X and Y each represent a hydrogen atom or together form a single bond, R ' 1 represents a hydroxyl group, acetoxy group, carboxymethoxy group or methoxycarbonylmethoxy group, R' 2 Represents a hydrogen atom, isoprenyl group, isopentyl group or propyl group, R ' 3 represents a hydroxyl group or a methoxy group, R' 4 represents a hydrogen atom, a hydroxyl group or a methoxy group, and R ' 5 represents hydrogen The atom, hydroxyl group, methoxy group or isopentyl group R ' 6 represents a hydroxyl group, a methoxy group or a carboxymethoxy group, and R' 7 represents a hydrogen atom or a methoxy group. 제1항에 있어서, 1-(2, 4, 6-트리히드록시-3-이소펜틸페닐-3-(4-히드록시-3-메톡시페닐)-1-프로판온, 1-(2, 4,6-트리히드록시-3-이소펜틸페닐)-3-(4-히드록시-3, 5-디메톡시페닐)-1-프로판온, 1-(2-카로복시메톡시-4-메톡시-3-이소펜틸페닐)-3-(4-메톡시페닐)-1-프로판온, 1-(2-히드록시-4-메톡시-3-이소펜틸페닐_-3(4-카르복시메톡시페닐)-1-프로판온, 1,(2-카르복시-메톡시-4,6-디메톡시-3-이소펜틸페닐)-3-(4-히드록시-3-메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4,6-디메톡시-3-이소펜틸페닐)-3,(3-히드록시-4-메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4,6-디메톡시-3-이소펜틸페닐) -3-(4-히드록시-3,5-디메톡시페닐)-1-프로판온, 2'-카르복시메톡시-4, 4 -디메톡시-3 -(3-메틸-2-부테닐)칼콘, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -이소펜틸칼콘, 3-(4-히드록시페닐)-1-(2, 4, 6-트리히드록시-3-n-프로필페닐)-1-프로판온 1-(2-카르복시메톡시-4, 6-디메톡시페닐)-3-(4-메톡시페닐)-1-프로판온, 1-[2-카르복시메톡시-4, 6-디메톡시-3-(3-메틸-2-부테닐)페닐]-3-(4-메톡시페닐)-1-프로판온,2 -카르복시메톡시-4, 4 , 6 -트리메톡시칼콘, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -(3-메틸-2-부테닐)칼콘, 2 , 4, 4 -트리히드록시칼콘, 2 -히드록시-4, 4 -디메톡시-3 -(3-메틸-2-부테닐)칼콘, 2 , 4, 4 , 6 -테트라히드록시-3 -(3-메틸-2-부테닐)칼콘, 2 -아세톡시-4, 4 , 6 -트리히드록시-3 -(3-메틸-2-부테닐)칼콘, 2 , 3, 4, 4 -테트라히드록시칼콘, 2 , 3, 4, 4 , 6 -펜타히드록시칼콘, 2 , 4, 4 , 6 -테트라히드록시-3 -이소펜틸칼콘, 1-(2, 4-디히드록시페닐)-3-(4-히드록시페닐)-1-프로판온, 1-(2, 4, 6-트리히드록시페닐)-3-(4-히드록시페닐)-1-프로판온,1-[2-아세톡시-4, 6-디히드록시-3-(3-메틸-2-부테닐)페닐]-3-(4-히드록시페닐)-1-프로판온, 1-[2, 4, 6-트리히드록시-3-(3-메틸-2-부테닐)페닐]-3-(4-히드록시페닐)-1-프로판온, 1-(2, 4, 6-트리히드록시-3-이소펜틸페닐)-3-(4-히드록시페닐)-1-프로판온, 1-(2, 4-디히드록시페닐)-3-(3, 4-디히드록시페닐)-1-프로판온, 1-(2, 4, 6-트리히드록시페닐)-3-(3, 4-디히드록시페닐)-1-프로판온, 1-(2-아세톡시-4, 6-디히드록시-3-이소펜틸페닐)-3-(4-히드록시페닐)-1-프로판온, 1-(2-히드록시-4, 6-디메톡시-3-이소펜탈페닐)-3-(4-메톡시페닐)-1-프로판온, 1-(4, 6-디히드록시-2-메톡시카르보닐메톡시-3-이소펜틸페닐)-3-(4-히드록시-페닐)-1-프로판온, 1-(2-카르복시메톡시-4, 6-디히드록시-3-이소펜틸페닐)-3-(4-히드록시페닐)-1-프로판온, 1-(2-히드록시-4-메톡시-3-이소펜틸페닐)-3-(4-메톡시페닐)-1-프로판온, 1-(3-이소펜틸-4, 6-디메톡시-2-메톡시카르보닐메톡시페닐)-3-(4-메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4, 6-메톡시-3-이소펜틸페닐)-3-(4-메톡시페닐)-1-프로판온, 1-(2, 4-디히드록시-3-이소펜틸페닐)-3-(4-히드록시페닐)-1-프로판온, 및 1-(2, 4, 6-트리히드록시-3-이소펜틸페닐)-3-(4-히드록시-3-이소펜틸)-1-프로판온 중에서 화합물을 선택함을 특징으로 하는 항궤양제.A compound according to claim 1, wherein 1- (2, 4, 6-trihydroxy-3-isopentylphenyl-3- (4-hydroxy-3-methoxyphenyl) -1-propanone, 1- (2, 4,6-trihydroxy-3-isopentylphenyl) -3- (4-hydroxy-3, 5-dimethoxyphenyl) -1-propanone, 1- (2-carboxoxymethoxy-4-meth Methoxy-3-isopentylphenyl) -3- (4-methoxyphenyl) -1-propanone, 1- (2-hydroxy-4-methoxy-3-isopentylphenyl_-3 (4-carboxymeth Methoxyphenyl) -1-propanone, 1, (2-carboxy-methoxy-4,6-dimethoxy-3-isopentylphenyl) -3- (4-hydroxy-3-methoxyphenyl) -1- Propanone, 1- (2-carboxymethoxy-4,6-dimethoxy-3-isopentylphenyl) -3, (3-hydroxy-4-methoxyphenyl) -1-propanone, 1- (2 -Carboxymethoxy-4,6-dimethoxy-3-isopentylphenyl) -3- (4-hydroxy-3,5-dimethoxyphenyl) -1-propanone, 2'-carboxymethoxy-4, 4-dimethoxy-3-(3-methyl-2-butenyl) chalcone, 2-carboxymethoxy-4,4,6-trimethoxy-3-isopentylchalcone, 3- (4-hydroxyphenyl) -1- (2, 4, 6-trihydr Cy-3-n-propylphenyl) -1-propanone 1- (2-carboxymethoxy-4, 6-dimethoxyphenyl) -3- (4-methoxyphenyl) -1-propanone, 1- [ 2-carboxymethoxy-4, 6-dimethoxy-3- (3-methyl-2-butenyl) phenyl] -3- (4-methoxyphenyl) -1-propanone, 2-carboxymethoxy-4 , 4, 6-trimethoxychalcone, 2-carboxymethoxy-4, 4, 6-trimethoxy-3-(3-methyl-2-butenyl) chalcone, 2,4,4-trihydroxychalcone , 2-hydroxy-4, 4-dimethoxy-3-(3-methyl-2-butenyl) chalcone, 2, 4, 4, 6-tetrahydroxy-3-(3-methyl-2-butenyl ) Chalcone, 2-acetoxy-4, 4,6-trihydroxy-3- (3-methyl-2-butenyl) chalcone, 2, 3, 4, 4-tetrahydroxychalcone, 2, 3, 4 , 4, 6-pentahydroxychalcone, 2, 4, 4, 6-tetrahydroxy-3-isopentylchalcone, 1- (2, 4-dihydroxyphenyl) -3- (4-hydroxyphenyl) -1-propanone, 1- (2, 4, 6-trihydroxyphenyl) -3- (4-hydroxyphenyl) -1-propanone, 1- [2-acetoxy-4, 6-dihydrate Roxy-3- (3-methyl-2-butenyl) phen ] -3- (4-hydroxyphenyl) -1-propanone, 1- [2, 4, 6-trihydroxy-3- (3-methyl-2-butenyl) phenyl] -3- (4- Hydroxyphenyl) -1-propanone, 1- (2, 4, 6-trihydroxy-3-isopentylphenyl) -3- (4-hydroxyphenyl) -1-propanone, 1- (2, 4-dihydroxyphenyl) -3- (3,4-dihydroxyphenyl) -1-propanone, 1- (2, 4, 6-trihydroxyphenyl) -3- (3, 4-dihydrate Hydroxyphenyl) -1-propanone, 1- (2-acetoxy-4, 6-dihydroxy-3-isopentylphenyl) -3- (4-hydroxyphenyl) -1-propanone, 1- ( 2-hydroxy-4, 6-dimethoxy-3-isopentalphenyl) -3- (4-methoxyphenyl) -1-propanone, 1- (4, 6-dihydroxy-2-methoxycarb Bonylmethoxy-3-isopentylphenyl) -3- (4-hydroxy-phenyl) -1-propanone, 1- (2-carboxymethoxy-4, 6-dihydroxy-3-isopentylphenyl) -3- (4-hydroxyphenyl) -1-propanone, 1- (2-hydroxy-4-methoxy-3-isopentylphenyl) -3- (4-methoxyphenyl) -1-propanone , 1- (3-isopentyl-4, 6-dimethoxy-2-methoxycarbonylmethoxyphenyl) -3- (4-methoxyphenyl) -1-propanone, 1- (2-carboxymethoxy-4, 6-methoxy-3-isopentylphenyl) -3- (4-methoxyphenyl) -1-propanone , 1- (2, 4-dihydroxy-3-isopentylphenyl) -3- (4-hydroxyphenyl) -1-propanone, and 1- (2, 4, 6-trihydroxy-3- An antiulcer agent characterized in that the compound is selected from isopentylphenyl) -3- (4-hydroxy-3-isopentyl) -1-propanone. 제2항에 있어서, 1-(2-카르복시메톡시-4-메톡시-3-이소펜틸페닐)-3-(4-메톡시페닐)-1-프로판온, 2 -카르복시메톡시-4-4 -디메톡시-3 -(3-메틸-2-부테닐)칼콘, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -이소펜틸칼콘, 1-(2-카르복시메톡시-4, 6 -디메톡시페닐)-3-(4-메톡시페닐)-1-프로판온, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시칼콘, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -(3-메틸-2-부테닐)칼콘, 1-(2, 4-디히드록시페닐)-3-(3, 4-디히드록시페닐)-1-프로판온, 및 1-(2-카르복시메톡시-4, 6-디메톡시-3-이소펜틸페닐)-3-(4-메톡시페닐)-1-프로판온 중에서 화합물을 선택함을 특징으로 하는 항궤양제.The compound according to claim 2, wherein 1- (2-carboxymethoxy-4-methoxy-3-isopentylphenyl) -3- (4-methoxyphenyl) -1-propanone, 2-carboxymethoxy-4- 4-dimethoxy-3- (3-methyl-2-butenyl) chalcone, 2-carboxymethoxy-4,4,6-trimethoxy-3-isopentylchalcone, 1- (2-carboxymethoxy- 4,6-dimethoxyphenyl) -3- (4-methoxyphenyl) -1-propanone, 2-carboxymethoxy-4, 4,6-trimethoxychalcone, 2-carboxymethoxy-4,4 , 6-trimethoxy-3-(3-methyl-2-butenyl) chalcone, 1- (2,4-dihydroxyphenyl) -3- (3,4-dihydroxyphenyl) -1-propane A compound characterized in that the compound is selected from on and 1- (2-carboxymethoxy-4, 6-dimethoxy-3-isopentylphenyl) -3- (4-methoxyphenyl) -1-propanone Ulcers. 다음의 일반식(Ⅰ )으로 나타내는 화합물Compound represented by the following general formula (I) 상기 일반식중, X' 및 Y' 는 각각 수소원자를 나타내거나 함께 결합을 형성하고, R'1은 히드록시기 또는 카르복시메톡시기를 나타내며 R'2는 수소원자, 이소프레닐기, 이소펜틸기 또는 프로필기를 나타내고, R'3은 히드록시기 또는 메톡시기를 나타내며, R'4는 수소원자, 히드록실기 또는 메톡시기를, R'5는 수소원자, 히드록실기, 메톡시기 또는 이소펜틸기, R'6은 히드록시기, 메톡시기 또는 카르복시메톡시기를 나타내고, R'7은 수소원자 또는 메톡시기를 나타내며, 만약 (1)R'2가 수소원자이며, R'4, R'4, R'5및 R'6중 적어도 하나는 메톡시기가 아니고, (2), R'2가 이소프레닐기이며, R' 1은 카르복시메톡시기이고, (3) R'2가 이소펜틸기이고 R'5와 R'7이 각각 수소원자이면, R' 는 수소원자이고, R'1및 R'6중 한가지는 카르복시메톡시기이며, (4) R'4가 수소원자가 아니면 R'3및 R'4는 일반적으로 히드록실기 또는 메톡시기를 나타내며, (5) R'5가 히드록실기이면, R'6은 메톡시기이고, (6) R' 가 에톡시기이면 R'6은 히드록실기이고, (7) R'6이 카르복시메톡시기이면 R'1은 히드록실기이다.In the general formula, X 'and Y' each represent a hydrogen atom or form a bond together, R ' 1 represents a hydroxy group or a carboxymethoxy group, R' 2 represents a hydrogen atom, isoprenyl group, isopentyl group or propyl A group, R ' 3 represents a hydroxyl group or a methoxy group, R' 4 represents a hydrogen atom, a hydroxyl group or a methoxy group, R ' 5 represents a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R' 6 Represents a hydroxy group, a methoxy group or a carboxymethoxy group, R ' 7 represents a hydrogen atom or a methoxy group, and if (1) R' 2 is a hydrogen atom, R ' 4 , R' 4 , R ' 5 and R' At least one of 6 is not a methoxy group, (2), R ' 2 is an isoprenyl group, R' 1 is a carboxymethoxy group, (3) R ' 2 is an isopentyl group, and R' 5 and R ' 7 If each is a hydrogen atom, R 'is a hydrogen atom, one of R' 1 and R ' 6 is a carboxymethoxy group, and (4) R' 4 R ' 3 and R' 4 generally represent a hydroxyl group or a methoxy group unless it is a hydrogen atom, and (5) if R ' 5 is a hydroxyl group, R' 6 is a methoxy group, and (6) R 'is an ethoxy group. time when R '6 is a hydroxyl group and, (7) R' 6 is a carboxy-methoxy group R '1 is a hydroxyl group. 제4항에 있어서, 1-(2, 4, 6-트리-히드록시-3-이소펜틸페닐)-3-(4-히드록시-3-메톡시페닐)-1-프로판온, 1-(2, 4, 6-트리히드록시-3-이소펜틸-페닐)-3-(4-히드록시-3, 5-디메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4-메톡시-3-이소펜틸페닐)-3-(4-메톡시페닐)-1-프로판온, 1-(2-히드록시-4-메톡시-3-이소펜틸페닐)-3-(4-카르복시메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4, 6-디메톡시-3-이소펜틸페닐)-3-(4-히드록시-3-메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4, 6-디메톡시-3-이소펜틸페닐)-3-(3-히드록시-4-메톡시페닐)-1-프로판온, 1-(2-카르복시메톡시-4, 6-디메톡시-3-이소펜틸페닐)-3-(4-히드록시-3, 5-디메톡시페닐)-1-프로판온, 2 -카르복시메톡시-4, 4 -디메톡시-3 -(3-메틸-2-부테닐)칼콘, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -이소펜틸칼콘, 3-(4-히드록시-페닐)-1-(2, 4, 6-트리히드록시-3-n-프로필페닐)-1-프로판온, 1-(2-카르복시메톡시-4, 6-디메톡시페닐)-3-(4-메톡시페닐)-1-프로판온, 1-[2-카르복실메톡시-4, 6-디메톡시-3-(3-메틸-2-부테닐)페닐]-3-(4-메톡시페닐)-1-프로판온, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시칼콘 및 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -(3-메틸-2-부테닐)칼콘 중에서 선택되는 화합물.The compound of claim 4, wherein 1- (2, 4, 6-tri-hydroxy-3-isopentylphenyl) -3- (4-hydroxy-3-methoxyphenyl) -1-propanone, 1- ( 2, 4, 6-trihydroxy-3-isopentyl-phenyl) -3- (4-hydroxy-3, 5-dimethoxyphenyl) -1-propanone, 1- (2-carboxymethoxy-4 -Methoxy-3-isopentylphenyl) -3- (4-methoxyphenyl) -1-propanone, 1- (2-hydroxy-4-methoxy-3-isopentylphenyl) -3- (4 -Carboxymethoxyphenyl) -1-propanone, 1- (2-carboxymethoxy-4, 6-dimethoxy-3-isopentylphenyl) -3- (4-hydroxy-3-methoxyphenyl)- 1-propanone, 1- (2-carboxymethoxy-4, 6-dimethoxy-3-isopentylphenyl) -3- (3-hydroxy-4-methoxyphenyl) -1-propanone, 1- (2-carboxymethoxy-4, 6-dimethoxy-3-isopentylphenyl) -3- (4-hydroxy-3, 5-dimethoxyphenyl) -1-propanone, 2-carboxymethoxy-4 , 4-dimethoxy-3-(3-methyl-2-butenyl) chalcone, 2-carboxymethoxy-4,4,6-trimethoxy-3-isopentylchalcone, 3- (4-hydroxy- Phenyl) -1- (2, 4, 6-t Hydroxy-3-n-propylphenyl) -1-propanone, 1- (2-carboxymethoxy-4, 6-dimethoxyphenyl) -3- (4-methoxyphenyl) -1-propanone, 1 -[2-carboxymethoxy-4, 6-dimethoxy-3- (3-methyl-2-butenyl) phenyl] -3- (4-methoxyphenyl) -1-propanone, 2-carboxyme A compound selected from methoxy-4, 4, 6-trimethoxychalcone and 2-carboxycarboxy-4, 4, 6-trimethoxy-3-(3-methyl-2-butenyl) chalcone. 제5항에 있어서, 1-(2-카르복시메톡시-3-이소펜틸-4-메톡시페닐)-3-(4-메톡시페닐)-1-프로판온, 2 -카르복시메톡시-4, 4 -디메톡시-3 -(3-메틸-2-부테닐)칼콘, 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3-이소펜틸칼콘, 1-(2-카르복시메톡시-4, 6-디메톡시페닐)-3-(4-메톡시페닐)-1-프로판온, 2 -카르복시메톡시-4, 4 -트리메톡시칼콘 및 2 -카르복시메톡시-4, 4 , 6 -트리메톡시-3 -(3-메틸-2-부테닐)칼콘 중에서 선택되는 화합물.A compound according to claim 5, further comprising 1- (2-carboxymethoxy-3-isopentyl-4-methoxyphenyl) -3- (4-methoxyphenyl) -1-propanone, 2-carboxymethoxy-4, 4-dimethoxy-3- (3-methyl-2-butenyl) chalcone, 2-carboxymethoxy-4,4,6-trimethoxy-3-isopentylchalcone, 1- (2-carboxymethoxy- 4, 6-dimethoxyphenyl) -3- (4-methoxyphenyl) -1-propanone, 2-carboxymethoxy-4, 4-trimethoxychalcone and 2-carboxymethoxy-4, 4, 6 -Trimethoxy-3-(3-methyl-2-butenyl) chalcone. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019880700971A 1986-12-12 1987-12-12 Anti-ulcer agents and novel chalcone derivatives containing chalcone derivatives as active ingredients KR890700117A (en)

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JP61-294952 1986-12-12
JP29495286A JPS63150241A (en) 1986-12-12 1986-12-12 Chalcone derivative and antiulcer agent containing said chalcone derivative as active ingredient
JP19819787A JPS6442422A (en) 1987-08-10 1987-08-10 Antiulcer agent
JP62-198197 1987-08-10
PCT/JP1987/000973 WO1988004288A1 (en) 1986-12-12 1987-12-12 Anti-ulcerous agent containing chalcone derivative as effective ingredient and novel chalcone derivatives

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